


Complicated Feelings of Love

by Darphrey4forevraftr



Category: Ever After High
Genre: Anal Fingering, Anal Sex, Angst and Fluff and Smut, Angst and Hurt/Comfort, Angst with a Happy Ending, Awkward Boners, Awkward Conversations, Awkward Kissing, Awkward Romance, Awkward Sexual Situations, Bi-Curiosity, Boys In Love, Boys Kissing, Bullying, Crying, Cuddling & Snuggling, Emotional Hurt/Comfort, Erections, F/M, First Time, First Time Blow Jobs, French Kissing, Friends to Lovers, Gay Male Character, M/M, Masturbation, Masturbation in Bathroom, Men Crying, Morning Cuddles, Morning Sex, Naked Cuddling, POV First Person, POV Male Character, Resolved Sexual Tension, Secret Relationship, Sex Talk, Sexual Content, Sexual Tension, Spooning, Stripping, Truth or Dare
Language: English
Status: Completed
Published: 2019-07-10
Updated: 2019-07-10
Packaged: 2020-06-25 15:20:23
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 10,140
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19748422
Author URL: https://archiveofourown.org/users/Darphrey4forevraftr/pseuds/Darphrey4forevraftr
Summary: When Daring and Humphrey play a sexual game of Truth or Dare, their both left with complicating affections for each other afterwards.





	1. Truth or Dare?

**Author's Note:**

> The whole story is told in Humphrey's point of view.

“Dare,” he chosen. 

"Daring, I dare you to take your pants off.” My roommate stood and shook his hips as he slowly undid his jeans. I could tell he was trying to dance seductively as his jeans slid down his legs to the floor. I’m not much of a dancer, but Daring seemed to have some moves, and everyone was cheering him on. Daring Charming was my chosen roommate this year at Ever After High and I didn't mind it in the least. He stepped out of his pants and sat back down, slightly red in the face. He was down to just his boxer-briefs now and was sporting a very noticeable bulge. Not that he was the only one in a state of undress though. We were playing truth or dare, and all of us were shedding clothes pretty quickly. 

I was down to my underwear too. I had a pair of briefs on and they were pretty tight. I was showing much more than I'd intended, and was a little embarrassed. We hadn’t set out to play truth or dare, but Daring l and had gone out to get something to eat, and bumped into Nina Thumbell and Madeline Hatter. They were roommates as well. After getting a quick bite and returning, we ended up back in their dorm room with another cute student, Apple White. I’ve had a crush on Apple since I met her at the freedom year orientation. Unfortunately, I’ve been too shy to have acted upon it. 

That’s the main reason I ended up in this game. I couldn’t pass up the chance to see Apple naked, or maybe even mess around with her! It had been Nina’s idea to play, and we had all been thought it sounded fun to do. Nina is very attractive and bitchy, and we've never personally clicked. All I know about her is she can shrink, she's the daughter of Thumbelina, and she's probably interested in Daring. Who could blame her? All the girls like Daring! He’s tall, athletic, and has striking dominate dark blue eyes. I’m not into guys, but even I know that Dare is really good looking! 

I’m his opposite in most every way. I’m skinny, shy, and am nerdy. I still have no idea why we were randomly assigned together as roommates, considering the strangeness of the pairing, but by some miracle, we really hit it off. I now consider him my best friend and we spend a lot of time together. He’s able to get me out of my shell, and I don’t think I would've been able to have had as much fun as I've recently had if it weren't for him. It was Daring’s turn now, and he looked around the room as he deliberated who to choose. Maddie was down to her bra and panties, as was Nina. I like Maddie, she’s got a bubbly personality and never once has had a bad thing to say about anyone. Nina isn’t as beautiful as her, but she has a nice body and a cute face. It was hard not to stare at her breasts that were barely contained by her bra. 

Apple currently had the most clothes on. She was wearing a EAH t-shirt, along with her bra and panties, but her skirt was gone. Apple’s long, blonde hair was pulled back in a ponytail. She always kept it down, so I considered it interesting seeing her curls up for once. I was hoping Daring would dare her to take her shirt off. I was dying to see her in only a bra. I tried not to stare as she stretched her creamy, pale legs and glanced at the clock. “One more hour guys, it’s getting late,” Apple noted. 

“Okay. Humphrey, truth or dare?” I was surprised that Daring had picked me. I thought I would be safe this round. I never imagined he would pick me instead of one of the girls. I was scared to death to be the first person naked. I’m incredibly insecure about my body, and I know I wouldn't have a chance competing with Daring. I’ve only been with one girl ever and that was Thronecoming on night. Melody asked me to dance with her and I'm sure that was because Sparrow danced with Blondie instead, but she was a nice girl, so I did. Maddie, Nina, and Apple were all pretty much out of my league and I didn’t want to relish in the fact of them laughing at me naked body. “Truth,” I told him. Nina snickered loudly and Apple just gave me an odd look. We were at the point in the game where almost everyone said dare. “Which one of these lovely maidens are you looking forward to seeing naked the most?” 

“Ummm…Apple I guess,” I answered, turning a deep crimson. Nina snickered again, but Apple smiled at me. I felt like finding a hole and hiding in it, I was so embarrassed! That smile from her, however, kept me in the game. It was my turn now, and I asked Apple if she picked truth or dare. 

“Dare, although I think I know what it’s going to be!” 

“Apple,” I stammered out, "I dare you to take your shirt off.” She smiled again and pulled her shirt over her head and tossed it to me. I missed it, causing it to sail pass my head, provoking another laugh from Nina. Right now, I only had eyes for Apple’s chest. She was wearing a red bra and the tops of her areola were visible. Her breasts looked perky and firm, and I soon hoped being able to see them without the bra on! My cock was so hard in my underwear, that I was scared I was going to cum! She winked at me and asked Maddie if she picked truth or dare. 

The game continued like this for the next fifteen minutes. Nina was the first one naked. Her body was spelltacular! She's small, tan, had blond hair and blue eyes. Every guy’s dream come true if you could get past her bitchy attitude. Her breasts were the smallest of the girls, but perfectly pear shaped. Her nipples were thick and very erect. She had a small patch of pubic hair above her pussy. Nina sat facing Daring, with her legs slightly spread, affording us a very good view. 

Maddie was the next to get naked, her breasts bouncing when her bra came off. They were of average size and her nipples were hardened, and her pussy was trimmed. She was obviously a little embarrassed, but laughed it off and dared Apple to take off her bra! 

She gave me another wink, reached behind her back, and undid her bra clasp. She stood, faced me, and pulled her bra off, then shook her tits in my direction. I almost came when I saw them. Her nipples were small, but hard. Her breasts were the perkiest I'd ever seen. Although to tell the truth, I hadn’t really seen that many naked breasts except in porn movies and magazines. Apple sat back down and asked Nina whether she wanted to pick truth or dare. 

She gave her a surprised look. Daring and I both had our underwear on still, and I was sure that she was going to have dared one of us to get naked. She didn’t look happy, but she said she would take a dare. 

“I dare you to make out with Humphrey for one minute." 

Everyone saw the look of revulsion on Nina’s face. It was obvious to everyone that she couldn’t stand me. My stomach turned. Kissing me was the most distasteful thing anyone could have dared her to do. I thought she was going to refuse, but then Daring spoke up. 

“Those are the rules of the game Nina. You can’t refuse a dare or you are out.” 

She stood up and angrily walked towards me. “Let’s get this over with nerd.” Her lips were on mine almost before the words were out of her mouth. I opened my mouth to kiss her back, but her lips were closed tight. Nina's flower scent smelled so sweet. This was the closest we had ever been to each other. Her lips were soft and I tried to slip my tongue in her mouth, but was rebuffed by her firmly closed lips. She was going through the motions, but had no intention of making this a real kiss. 

That pissed me off! I’ve never done anything to Nina, and in fact, I have always tried to be nice to her. Why did she hate me? Why did she want to embarrass me and make me feel like shit? I heard Apple say thirty seconds left. Our lips were still touching, but there was no passion there. Fuck it, I hadn’t asked to be put in this situation, but I would make the most of it. I reached up and cupped Nina’s breast. She gasped in shock and my tongue slid into her mouth. She started to pull back, but failed as I held her close. She squirmed and I pinched her nipple. 

“Time's up,” Apple claimed between her laughs. 

Nina pulled back and gave me a dirty look, but everyone else was laughing. I felt like I had finally won against this bitch. She sat back down and looked around the room before her eyes settled back on me. “Man enough for a dare yet Humphrey?” 

We were all going to get naked, so I might as well get it over with now. I was still feeling really good about myself after turning the tables on Nina. “I’ll take a dare,” I said grinning. “Let me guess, you want another kiss?” The rest of the group howled in laughter while she only scowled at me. 

“No, I think it’s time for the boys to get nude.” I had known this was coming and stood to pull off my briefs. “Humphrey, I dare you to take Daring’s boxers off with your teeth.” 

What the fuck did she say? Take off my roommates boxers with my teeth? No way! 

“That’s not fair Nina, Daring isn’t involved in this dare.” 

“Not true at all, we are all playing the game. Apple dared me to kiss you and I did it. Now your dare is to take off his boxers with your teeth.” 

“She has a point,” Apple remarked. Though not further adding to the matter, Maddie nodded in agreement. I looked at Daring and he looked just as uncomfortable as I did. 

Then, he stood up. 

“Let’s get it over with."

My only choices were to go through with the degrading dare or look like a wimp and quit the game. Apple gave me a smile in support, and that gave me the courage I needed. I got down on my hands and knees in front of Daring, and leaned forward until I could get the elastic band of his boxers in my mouth. I bit down and tried dragging them off. I could feel the bulge of his cock against my cheek and did my best to ignore it. Slowly, his boxers began to slide down. I tugged with my teeth again and pulled them down far enough that Daring’s cock popped out and slapped me in the face. 

I fell back onto my ass in shock. I could hear laughter all around me. Once again, I turned a deep red. He squeezed his legs together, causing his boxers to fall the rest of the way to the floor. I silently thanked my friend for sparing the ordeal of having to finish the job. I tried getting to my feet, but couldn’t take my eyes off of his big dick. I had no idea that he was so large! Daring’s cock was a lot bigger than mine, and thicker too. The head of his penis was a deep shade of pink, and I was close enough that I could see that he shaved his balls and trimmed the rest of his pubic region. 

The group was still laughing when I finally came to my senses and scrambled back to where I was sitting. I don’t think anyone had seen me staring at Daring’s cock. Well, I hoped not at least. I willed myself to look away from him, instead forcing myself to stare at Maddie’s breasts, then Apple’s, but I couldn’t get his dick out of my mind. What was going on with me? I’m not gay and I’ve never had any interest in men, so why was I so fascinated by my friend’s penis? 

It was my turn to dare someone and I picked Apple. She quickly said dare, and I told her to take off her panties. Now I was the only one with my underwear on. Everyone stared at her as she took her panties off. My embarrassment had been forgotten for a moment. She was completely shaved, and I could see her puffy lips were already visibly wet. 

Apple sat down and picked me for a dare. I knew I had to get naked, and I knew that she wouldn’t be mean to me like Nina, so I accepted the dare. “Take off your underwear Humphrey. Show us what you’re hiding!” 

I took off my briefs and endured the stares from the group. I was feeling self-conscious, knowing I was nowhere near Daring's size. My cock is about six inches and not nearly as thick as his. I had trimmed up the other day and was glad with my decision. 

“That’s pretty pathetic, you call that a cock? Look at it next to Daring’s!” Nina laughed. 

Maddie looked fairly uncomfortable, and Apple was giving Nina a dirty look, but it was Daring who came to my defense. “Leave him alone, we are supposed to be having fun here. We’re all friends, and if you’re going to be rude to anyone, then me and Humphrey are going to leave!” 

Nina apologized to Daring, and then me, although it was obvious that she didn’t mean what she said. I shrugged it off and dared Maddie to do some naked jumping jacks. The game continued like that. Mostly innocent dares like spread your legs, bend over, show your asshole, things of that sort. Apple dared Daring to suck on Maddie’s nipples, and Nina looked slightly jealous, but besides that, the game had settled down into naked, innocent fun. 

“Truth or dare Humphrey?” Nina asked me. 

We were down to the last five minutes of the game and I couldn’t pick truth. I sighed and hoped it would be another easy dare. Apple had just fingered herself in front of us, so maybe it would be something kinda like that. 

“I dare you to suck Daring’s cock for one minute!” I tried to stammer out an objection, but she was already arguing that everyone else had done their dares and it wouldn't be fair for me to back out. 

“Humphrey, I dare you to suck Daring’s dick!” Nina exclaimed again loudly. 

The room went dead silent. I could hear my heart pounding in my chest. Surely, he would object to this! I looked at my roommate, him just staring back at me expectantly. Everyone knew the rules, you couldn’t turn down a dare! Nina laughed and looked really proud of herself. I looked at the only other girls in the room, Apple and Maddie, but saw no support from them. I was trapped. I took a deep breath and moved closer to my roommate. I got down on my knees in front of him, his cock pointed at my face, almost menacingly. I couldn’t do this!

“Come on Humphrey, it’s just a game,” Daring remarked. 

His cock looked huge up close. I inhaled his musky scent. There was no getting out of this, and I was going to have to do this. My heart was racing and my palms were sweaty. Though ashamed to admit the truth, my dick was hard. I leaned in closer to Daring’s cock, opening my mouth and sticking out my tongue. Right before I made contact, I closed my eyes. 

My tongue touched the head of his cock. It felt weird: soft and spongy. My tongue danced along the tip hesitantly, tasting his pre-cum, and it wasn’t bad. Salty, but it didn’t gross me out. I willed myself to open my mouth wider and take Daring into my mouth. His cock slid in slowly. I felt the head enter my mouth, then inch after inch of his hard shaft. The head laid on my tongue at the back of my mouth. I tried to get more of him in my mouth, but felt like I was going to gag. My lips closed around his shaft and I sucked. 

I heard a moan escape from my him. My nervousness was gone, replaced by total desire to satisfy my friend. I sucked on his dick and slowly pulled back until just the head of his cock remained in my mouth. Then, I took him into my mouth again, before slowly sliding him out. Daring’s hands were on the back of my head as I bobbed on his dick. He moaned again. My own cock felt like it was about to explode. I couldn’t believe I was giving my roommate a blowjob! 

His cock was sliding in and out of my mouth faster now, and I started to wonder how long it would take him to come and what it would taste like. “Humphrey!” I heard Apple shout, breaking my concentration and taking me out of the moment. Daring pulled his cock out, and I turned to look at the girls, totally bewildered. 

Nina was in hysterics. She was struggling to say something, but was laughing too hard. Apple looked pissed off, and Maddie was trying to hold back her giggles. “Didn’t you hear us call the time?” she wondered. “You only had to blow him for a minute!” 

Nina was laughing so hard that tears were coming out of her eyes. “He didn’t want to stop!” she wailed. I looked up and Daring wouldn’t meet my gaze. This was all most likely embarrassing for him, and it wall all because of me.

“Sorry, I didn’t hear anyone say anything.” 

“Seriously? You blew him for almost three minutes! I kept telling you time was up over and over again!” 

“Sorry Apple,” I said sheepishly. I hadn’t thought it was possible to be more embarrassed than I had earlier in the night, but this by far took the cake. I had gotten so into blowing my roommate, that I didn’t realize the minute was up. Nina was still giggling, and now, Apple was giving her angry looks. I had never seen her mad before. A part of my mind processed the fact that she must've liked me, otherwise, she wouldn’t be so upset right now. I was so embarrassed that it was hard to take in any solace. 

“I think it’s time to call it a night,” Daring firmly told us. Apple quickly started getting dressed and Maddie followed suit. Nina started to say something, but he gave her a dirty look, and she silenced her mouth. I gathered my clothes and turned my back on the group while I dressed. 

I was never going to be able to live this down. 

“You ready to go?” Daring asked me. I nodded my head and mumbled a goodbye to the girls. What was I going to say to him when we got back to our room? How could I explain how carried away I had gotten? I didn’t even understand it myself!

We walked back to our dorm in silence. The full weight of what had happened was hitting me now. I had blown my best friend - and I had enjoyed doing it! I had gotten so carried away, that I blew him for far longer than the dare required. I knew Daring was mad, but I hoped he wouldn’t end our friendship over it. I had only sucked his dick because Nina dared me, and he had even said himself that it was only a game. I enjoyed sharing a dorm with Daring and having him be my friend, but what if he wanted a new roommate now? What would I do? 

We got back to our room, and he stripped out of his clothes, climbing into bed. I tried not to stare at his muscular body. I tried not to notice the bulge in his boxers, and especially, remember what was behind that bulge. I quietly stripped down to my briefs and climbed into my bed. I wanted to apologize, but I wasn’t sure what to say. 

“Are you doing okay?” Daring asked. 

“Yeah, just thinking.” 

“Crazy night, wasn’t it?” 

“It was, listen sorry…” 

“Don’t,” he barked. “Seriously don’t, it was a game and it’s not a big deal. Besides, it felt pretty good.” 

I gave a nervous laugh before asking, "Really?”

“I hate admitting it, but that was the best blowjob I’ve ever had.” 

I swelled with pride realizing I was being complimented on my ability to suck cock. I’ve never had a gay thought in my life, and even though I got carried away earlier, it had only happened because I had been dared. 

“Don’t worry about Nina and the girls, they won’t say anything and I’ll make sure they don’t tease you. If they do, I'll deal with them personally.” 

“Thanks, I appreciate it.” 

“Can I ask a favor though Humphrey?” 

“Of course,” I told him. “You’re my best friend, you can ask me anything!” 

“Truth or dare?” 

I was confused, but I heard myself answering with dare. 

“This is embarrassing, but the whole game really got me excited. I don’t want to get blue balls and…I was wondering…umm, would you mind finishing me off? I dare you to.” 

Did he just ask me what I think he did? There was no way, I must've been hearing him wrong. 

“Finish you off? Like how?” 

“I was hoping you could finish blowing me. Godmother, I feel weird saying that out loud. But Humphrey, it felt really good and I need to cum. I won’t tell anyone, can't you just do it this one time, please? Finish what you started?” 

My head spun. Daring was asking me for a blowjob. This wasn’t the game anymore. This was my roommate and my best friend, asking me to suck him off. I was surprised to feel my cock getting hard. I couldn’t believe that the idea of blowing him again was arousing me so much. I wasn’t sure what to do, I didn’t want him to think I was gay, but I also didn’t want to let him down. 

“I guess I can do that,” I told him as I climbed out of my bed. He threw off his covers and pulled his boxers down. His dick was pointing straight up in the air. I got into bed with him and before I knew it, I had his cock in my mouth again. 

It was a familiar feeling now, his cock sliding in and out of my mouth. Daring’s hand rested on my head again, and I found that comforting. I used my tongue as much as possible, rewarded by moans of encouragement from him. I grew brave and cupped his balls in my hand. They were bigger and heavier than mine, and odd to touch. I gently squeezed and rolled them between my fingers. 

Daring moaned loudly and pushed my head down, jamming more of his dick in my mouth than I had taken before. I tried not to choke as his cock rammed down my throat. Just when I thought that I couldn’t take down anymore, Daring relaxed his grip on my head and I pulled up, sliding his cock out of my mouth completely. Catching my breath, I kissed his tip and took him inside of me again. Now that I knew I could deep throat him, I repeated the action. 

Daring was moaning and wiggling around. I kept blowing him and playing with his balls, while grinding my dick into his bed. I was so hard! Who would have thought that sucking cock could be such a turn on? “Oh yeah Humphrey! I’m about to cum, keep doing that!” 

I sucked furiously, Daring beginning to buck his hips. His body suddenly stiffened and I heard a loud groan, then my mouth filled with his cum! There was so much, that I almost choked on some. I swallowed up as much as I could, and finally his cock quit erupting. I released it from my mouth, licking the rest of the cum that settled upon my lips. Daring tasted amazing! The saltiness had a very appealing taste. 

Embarrassment hit me knowing that once again, I had gotten really engaged into giving Daring a blowjob! He was smiling and had a content look on his face. “Thanks Humphrey, I really needed that.” 

I mumbled that it was no problem and went back to my bed. He pulled his covers up and rolled over. Meanwhile, I lay on my bed wondering what had happened. Was I gay? No, I had just helped out my friend. That was it. My cock was still rock hard in my briefs, and I needed relief. I didn’t want Daring to hear me masturbating, so I went to the bathroom and locked myself in, taking my underwear off. 

My briefs were slick with pre-cum, and I was surprised that I hadn’t blown my load earlier. I closed my eyes and pictured Apple’s tits. I remembered what it was like kissing Nina and feeling her up. I thought of Maddie’s breasts and tried to imagine sucking them. I stroked faster, needing to cum badly. Visions of breasts dissolved and I pictured Daring’s huge cock. I remembered how it throbbed and how it filled my mouth. I remembered the taste of his semen. 

I groaned loudly as I came in some tissue paper I had grabbed. My cock spasmed and I I shot load after load. I don’t remember ever having an orgasm as intense as this. I cleaned myself up and wondered what was happening to me. Why had I pictured Daring’s dick? Why couldn’t I stop thinking about blowing my roommate? 


	2. Confrontations

**Summary for the Chapter:**

> I made this the shortest chapter, but the next one will make up for it!

Daring was gone when I woke up in the morning. I stood in the shower for a long time trying to process what had happened. Would things be weird between us now? Could everything return to normal? Did I even want it to return to normal? I didn’t see him until dinner. The events of the night before didn’t come up at all. It was a little awkward for me at first, but by the end of dinner we were laughing and joking like nothing had ever happened between us. 

I had an early tech club meeting on Monday, and Daring was asleep when I woke up. We didn't see each other until that night, but I did hear from Apple however. She sent me a hext and wanted to know if I was interested in hanging out with her on Thursday. My heart raced. She was interested in me! I told Daring and he congratulated me. “Just play it cool,” he advised me. “You know she likes you now, and you’ve already seen her naked, so there is nothing to be nervous about.” 

We had a science and sorcery test on Wednesday. I spent the next two nights immersed in my hextbooks, taking breaks only to getting something to eat with Daring, or having or to reply back to the occasional hext from Apple.

* * *

When I got back to my dorm after school on Wednesday, Daring was waiting by the door. “You studied hard for that test, let’s celebrate!” he announced. He had the same test, but he hadn't studied as much as me. I was happy and relaxed, things couldn’t get any better. I was sitting next to my best friend playing video games and had a date with my crush the next day! 

I was so focused on the game, but looking to my side, I became conscious of how close Daring and I were sitting next to each other. Our shoulders were touching. There wasn’t a lot of conversation, because of how immersed in the game we were, but I could smell his cologne. That prompted a stirring in my pants, and thoughts of sucking him off flooded my brain. Why was I thinking about this again, and why was I getting so aroused? 

I shifted myself, breaking contact with Daring and hopefully concealing my rapidly growing erection. He didn’t seem to notice and finally my dick settled down. When I went to sleep that night, it was visions of Daring in my dreams though, not Apple.

* * *

Apple and I met in Book End and headed to the Hocus Latte Café. Conversation flowed easily and every time I started to get nervous, I just remembered what Daring had told me. We’ve seen each other naked already and she asked me out. She likes me! There truly was nothing to be shy about. 

“I crownloaded some new movies, want to come back to my room and watch them? Briar is going to a party tonight, so she'll probably be back late. Nobody will bother us.” 

“Sure thing!” My heart was racing as Apple and I walked across campus together. I had been imagining this moment all year long. She was inviting me back to her room alone! _Please Godmother_ , I thought, _don’t let us bump into Nina in the hallway_! We lucked out and made it into Apple's dorm room without ever seeing her. 

She scooted close to me on the bed and in an attempt at making a bold move, I put my arm around her. She didn’t mind. Instead, her head settled against my shoulder. 

“Mind if we lay down? It would be more comfortable.” 

I swallowed hard before telling her that sounded fine. My pulse was racing. Apple laid down in front of me, and then I pulled my arms around her. I could smell her hair. It smelled like apples. The movie continued on in the background, and I tried to figure out what to do next. How do I make a move? Should I just let her make the next move? No, girls want a confident man! 

I leaned closer and kissed her neck, Apple squeezing my hand in return, and I continued the same move softly again. She rolled over, staring into my eyes, smiling. We both kissed. Her lips were soft and her mouth tasted as sweet as candy. Apple's tongue darted into my mouth, playfully wrestling with my tongue. My arms were around her and I pulled her closer to me. 

My cock was fully erect. I was incredibly turned on by her. She broke the kiss and smiled at me again. I felt her hand on my butt. She squeezed each cheek, then slowly moved around to my front. I almost came when Apple’s hand brushed across my penis. Things were moving so fast. I cupped her breasts. They felt so squishy in my hands. She broke the kiss again, this time pulling her shirt off and undoing her bra. I had seen the sight of breasts during the game of truth or dare, but it was so much better seeing them when it was the two of us alone. I ran my hands across her naked skin. Her nipples stood at attention. Apple kissed my neck, while I played with the tits I had fantasized about for months. 

She tugged at my shirt and I took the hint, undoing my suspenders and pulling it off. She kissed down my chest until she came to my belt buckle. Her eyes met mine and she gave me that sexy smile again as she undid my belt, unfastening my pants and taking them down. My briefs came off next, my dick springing about, and I had no idea what to say. My mind was spinning! Apple held my cock in her hand. She licked up and down, over and over. I closed my eyes as she started to suck me off. It felt like electricity was shooting through my entire body! 

Daring was sucking my dick…wait, why was I fantasizing about him right now? Apple, my dream girl, was blowing me, yet when I closed my eyes, it was my roommate I pictured. She fondled my balls and sucked my cock harder. It felt pleasuring, but wrong. It should be Daring Charming instead. Why was I even thinking like this? What the hell was happening to me? I pictured his muscular chest, his smile, his dark eyes. My erection was quickly disappearing. I was freaking out so much, that all I could think about was my roommate. Apple looked up at me, alarmed at why I was losing my hard-on. I closed my eyes and tried to remember every fantasy I had ever had about her. 

She doubled her efforts at blowing me, but it was no use. My erection was gone. Finally, Apple released my limp dick from her mouth. “Everything okay?” she asked. 

“I’m sorry, I don’t know what’s happening.” 

“It’s okay Humphrey, it happens to all guys sometimes.” She scooted and snuggled against me, her breasts squished up against my chest. “We can just watch the movie, it’s cool.” Apple rolled over to face her mirrorpad again. She put my hand over her breast and I could feel her hard nipple, but it did nothing for me. 

I tried to concentrate on the movie, but all I could think about right now was Daring. 

What was he doing right now? Was he thinking about me? Did he ever think about what happened last weekend? I was still naked, and I was starting to feel self-conscious because of the thoughts that suddenly flooded my brain. 

I pulled away from Apple and grabbed my pants. 

“I’m sorry, I have to go.” 

“You sure everything is alright?” 

I could hear the concern in her voice and all I could do was nod. “Yeah, I’ll explain later. I just have to go now.” I fumbled with my clothes while Apple watched me. What was I doing? Here is the girl I have lusted after an entire two years, laying topless on the bed in her dorm room, and I was leaving? I didn’t understand any of this at all, but I knew I had to see Daring.


	3. True Love

**Notes for the Chapter:**

> This is the last chapter, enjoy!

Daring was looking at himself in one of his many hand mirrors when I got back to our shared dorm. “How was your date?” he asked me. 

“It was okay.” 

“You’re back early, I thought you would be out with Apple for at least a bit longer.” 

“About that...I have to tell you something, but you need to promise you won’t make fun of me.” 

Daring set down the golden mirror and gave me his full attention. “Humphrey, have I ever made fun of you? You can tell me anything. You know that, we're friends!” 

“I know,” I told him. “But this is pretty weird, and I’m not even sure how to explain it.” I sat down on the edge of my bed and tried to gather my thoughts. “Okay, I was out with Apple, and everything was going great. We went back to her room and started fooling around. She got topless and took off my clothes. 

Daring was grinning now. “Go on,” he suggested. “What happened next?” 

“She started to blow me, but then it got weird. I couldn’t do it.” 

“Why? What happened?” 

“I can’t explain it, I just can’t.” 

I was starting to shake. How did I tell him what had gone through my mind? “One second Apple was blowing me, and then the next, I realized that she's not what I want at all!” 

I started to cry, not knowing how to say what I was feeling, and I didn’t know what his reaction would be. He quickly jumped up from the floor and sat on the bed next to me. Daring put his arm around me and I collapsed into his chest. I couldn’t stop sobbing, but he just held me and gently rubbed my back. 

“It’s okay, you're okay Humphrey.” He held me tightly until I finally got myself under control. I sat up and wiped away my tears. He was so close to me now, his face just inches from mine. My stomach was in complete knots, and if I told Daring what I was thinking, he might never speak to me again. “It’s okay Humphrey, you can talk to me. You know that you can tell me anything you want, right?” 

I nodded and tried to gather my thoughts. Daring’s hand was on my shoulder and he gave me a reassuring squeeze. “What happened with Apple? Why did you realize that she wasn’t what you wanted?” 

“I don’t know how to say this. It was fine, she was blowing me, but when I closed my eyes, all I saw was you. Don’t hate me Dare, but I think I’m in love with you!” 

The shock was evident on his face and I was scared that I had lost my best friend. 

“Why do you say that?” 

“Ever since what happened last week, all I can think about is you. I loved sucking your dick and when Apple was sucking mine, I was wishing it was you. I’m sorry, I know that is so gay, but I’ve never liked any guy before. I don’t know why, but I just can’t stop thinking about you. Please don’t stop being my friend, I'm really sorry.” 

I was rambling now, repeating the same things, but he put an end to it. He leaned in and kissed me tenderly. Daring’s lips were rougher than Apple’s. His tongue pushed against my mouth and without thinking, I opened up and let it in, his tongue exploring me. It was rough, but gentle at the same time. I kissed him back and inhaled the scent of his strong cologne. My penis came to life and it felt like the electricity was shooting through my body once again. 

Without saying a word, Dare broke our embrace and dropped to his knees on the floor in front of me. He undid my belt and removed my pants. I was still in complete shock, especially when I felt the warm wetness of his mouth on my cock! 

I started to come back to my senses. How had this happened? Is this what I wanted? Was Daring gay? Was I gay? I tried to force all these questions out of my mind, trying to just enjoy the moment. He had taken me completely into his mouth. His tongue was against the underside of my shaft as he pulled his head back, then went down on me again. His face brushed against my thigh. This felt so different from Apple’s blowjob. 

I closed my eyes half expecting my thoughts to turn to her this time. That’s how confused I was. Thankfully, it was Daring that occupied my thoughts. He was the first cool guy who had ever taken me as a friend. He treated me like an equal instead of the underdog I formerly was before we met, always trying his best to include me in whatever he was doing. He never laughed at me when I did something awkward, and was always being supportive. 

I ran my fingers through his locks. Daring had one hand on the base of my shaft, jerking it off as he sucked. The other hand was caressing my leg. I couldn’t hold out any longer. My best friend was giving me the best first blowjob ever. I warned him that I was about to come, and he doubled his efforts. My balls were tingling and tightening up. I felt a tremble go up my leg, and then my cock exploded in his mouth. I let out a loud moan as I came. 

Daring swallowed it all, his tongue sweeping up my shaft and getting every last drop of cum. Totally spent, I fell back on the bed. 

Shit, had this really just happened? 

He climbed onto the bed next to me. “How was that?” he asked. I tried to form an answer, but he kissed before I could. There was a tangy, salty taste to his mouth now. It took me a second to realize that I was tasting myself. My tongues swirled around his, and my hand found its way to his smooth, hard chest. I ran my hand across his chest, then drifted down to his massive bulge. I had forgotten how big Daring was! I wanted to satisfy him. Make him feel as good as he had made me. 

My lips left his mouth and trailed down his neck. His shirt was off, and though had not remembered that happening, I gladly kissed his chest. I licked, sucked, and kissed his nipples. My tongue flicked one of them. It'd been smaller than any other girl’s nipple I've seen. He gave a contented sigh. I made sure to give equal attention to both of his nipples, moving down again. I kissed the abs across his stomach, and made my way to his waist. He was only wearing a pair of jeans, and I quickly took them off.

Just like in the game of truth or dare, his cock sprang out. This time instead of the embarrassment, all I felt was raw hunger. I licked the side of his cock all the way up to the dark pink head. My tongue flicked across his head, and Daring moaned encouragement. “Humphrey, that feels good. Make me cum.” I opened wide and took in as much of his monster cock as I could. His hands were on my head. His dick hit the back of my throat, and I tried to force more of him inside me. 

I was about to choke, but I eased up and his cock slid out of my mouth. I loved the feeling of Daring’s fingers in my hair. I kissed his dick, and licked down the shaft to his balls. I took the first in my mouth, then the other. My hands went to his behind, and I planted them on his ass. I couldn’t believe how firm it was!

I kissed back up to his cock, slurping my way down. “Suck me off, I want to cum in your mouth again.” I took Daring into my mouth, bobbing my head up and down, him moaning loudly in the background. My hands squeezed his perfect, tight ass. I could feel his muscles twitch and I knew he was going to cum soon. His fingers grabbed my hair and he held my head into place. 

"I’m going to cum Humphrey! I’m going to fucking cum!” I let him fuck my face, opening as wide as I could and making sure my tongue never stopped working his cock. Daring thrust his hips at me one last time, and then let out a loud groan, filling my mouth with his hot cum. I swallowed, savoring the taste of my friend. I milked him dry before kissing him once more. We kissed and cuddled until we finally fell asleep, naked in each other’s arms.

* * *

I woke up the next morning, feeling warm and content. Daring was still in my bed, spooning me. I lay there thinking of what had happened, processing everything and wondering what it meant. He began to stir, so I rolled over to face him. He smiled at me and said, “Good morning.” 

“Good morning to you too. Are you okay with what happened?” 

“Yes,” he asserted. “Why wouldn’t I be? I like you, and I'm also attracted to you.” 

“I never knew you were gay.” 

“Humphrey, I don’t believe in straight or gay. People are people, and you are a person that I really like. I didn’t realize you felt the same until recently, but I’m glad you do.” 

“Have you been with another guy before?” 

“No,” Daring said shaking his head. “I spent the summer with Hunter, and we experimented. It was mainly handjobs that I gave him, and we never did any kissing. Speaking of which…” He leaned in and kissed me on the mouth. I felt butterflies in my stomach as I kissed him back. This was incredible, I don’t remember ever feeling such happiness. 

“We’ve gotta get going. I don’t know about you, but I’ve got some important things I've got to do today.” Daring kissed me one more time before getting out of bed, gathering up his clothes to go to the shower. 

“Humphrey, for now, let’s keep this all to ourselves. I care about you, but neither of us need to be the center of the school gossip mill. Especially if Blondie found out, you know how she is.” 

I agreed with him. I had been teased and picked on my entire life for not only my body and nerdy ways, but also for my name and story. I didn’t want to endure more bullying because I had found someone I loved. Did I really love Daring? I thought about it throughout the day, and concluded that I had. He had already proved himself a good friend. He cared about me and was far too good if I were to say so myself. There was no denying that I was attracted to him. I got hard every time I thought of his athletic body naked. 

* * *

That night, we slept together again. Nothing happened besides kissing, but it felt nice to be in Daring’s arms. I loved the feeling of his warm body next to mine. I knew I was safe, and nothing could possibly hurt me. 

In the morning, to my surprise, I woke up with my cock in his mouth. At first, I thought it was a dream, an incredibly hot and sexy one. The cobwebs started to clear from my mind as I realized it was reality. Daring had woken me up with a surprise blowjob! 

I started to sit up, but his hand pushed down on my chest. My gaze met his and he gave me a wink. It was so hot to see my newfound lover sucking on my cock. I’m not sure how long he had been at it, but I was about to cum. Dare was rubbing my chest with one hand and the other started playing with my balls. I couldn’t take it anymore, and I let out a yell as I came in his mouth. He swallowed the cum and grinned at me. 

“Good morning!” 

“Great morning you mean, that was the best way ever to wake up!” 

“Glad you liked it, but I’ve got to run to class now.” He gave me a quick kiss and grabbed his books for class. I laid in bed with a silly grin on my face until I remembered I had class also. I jumped out of bed, raced to the shower, and barely made it to class on time. 

* * *

Wednesday night, Daring was working on a paper. My studying was done for the night, but I knew he had a long night ahead of him. I stood behind him as he worked at the desk, giving him a small peck on the cheek. Massages weren't my strong suit, but I knew Daring was tired, so I gave him the best shoulder rub that I could manage and was rewarded with a big smile. 

“I wish we had realized our feelings sooner,” he told me. “We wasted an entire semester. Let’s not waste any more time.” 

“I’m so happy with you, but it wasn’t wasted time. It was great getting to know each other and develop our friendship." 

“I know that, but I’m ready to take things to the next level.” I wasn’t sure what Daring meant and he could see the confusion on my face. “Humphrey, I want to have sex with you, and I want you to fuck me too. What do you think?” 

Honestly, full blown sex hadn’t even crossed my mind. I was so happy with where we were at already. Occasional handjobs and a lot of blowjobs were great. Even better was the kissing and cuddling, the kind of intimate moments you only experience with a real lover. The thought of anal sex scared me and excited me at the same time. I wanted to experience everything with Daring. I wanted to make him happy, but could I go that far? His dick was so big, I wondered if it would hurt or if I would enjoy it? 

He was watching my face as I struggled with these thoughts. “It’s okay if you want to go slow. I love you, and eventually, I want to have sex with you.”

"We're not officially together yet." 

"Of course we are." 

"I meant are we like, you know, boyfriends now? You never really asked yet." 

"Well then, let me take a step back then. Do you want to be my boyfriend?" 

"Yes!" 

I made my decision on the spot when he said the L word. “I love you too Daring. I want everything with you." With him now being my boyfriend, I felt I could take on anything. 

"Let's do it now!” 

“Hold on, not this second,” he laughed. “I have to finish this paper! Besides, we need to prepare ourselves for it.” I wasn’t sure what he meant by preparing for all of this. I was still really naive when it came to the sexual things, but I shook my head in agreement. 

“Let’s do it Saturday night. We'll make a special night out of it. I’ll pick up some things and we can order take out. A special romantic night for the two of us," Daring explained. 

The grin on my face was a mile wide. I was still nervous at the thought of him fucking me with his huge dick, but I was also turned on. I looked down and could see a bulge in his pants. I guess I wasn’t the only one excited about this. 

“Saturday night it is! You finish your paper right now. Don’t mind me, I’ll just be under the desk.” Before he could say another word, I climbed under the desk and undid his jeans. He raised out of the chair so I could pull them off. “Work on your paper, leave this to me!” 

“I’ll try,” he laughed. “But I’m not sure how well I’m going to be able to concentrate!” Daring went back to typing and I began playing with his cock and balls. I kissed his thigh and slowly stroked him. He was so big! How would that fit in my ass? He was fully erect now and I kissed up his thigh until I came to his balls. I licked them, sucking on each ball. I could hear the computer keyboard clicking away over his moans. I hoped his paper turned out good! 

Grasping the base, I lowered my head and took him in my mouth. I sucked slowly, wanting to prolong this. I couldn’t hear him typing anymore, so I stopped and told him to get back to work. The typing resumed, and I resumed blowing him. By now, I was very familiar with the taste and texture of his penis. I sucked on him, flicking my tongue across his cock. He moaned again and scooted forward in the chair. Slowly, I took more of Daring into my mouth until his penis was as deep into my throat as it could be. It was hard not to gag, but I knew that he loved when I deep throated him.

“Humphrey, baby, keep that up!” 

I swirled my tongue around and he moaned again. I squeezed his balls gently and started sucking harder. Daring was squirming now and the typing stopped. He knew it turned me on when he pulled my hair. I sucked and he pulled. I was hard, and with one hand, I started rubbing myself. 

I pulled off until just the head was in my mouth, my tongue overly stimulating it. He was moans were loud and his hips were starting to move fast. It wouldn’t be long now before I tasted him again. I kept stroking his shaft, my tongue continuing the teasing of his head. “Fuck, I’m going to cum! HUMPHREY!” he screamed out. I kept stroking him until he came, my mouth filling with cum. I didn't let a single drop go to waste. 

When he was finished, I kissed the head, pulled his jeans back up for him, and climbed out from under the desk. “You better get an A,” I joked. 

He chuckled, “I hope so, I need it. Let me take care of you first.” 

As much as I wanted him to relieve my hard-on, I told him no. “Work on your paper, I just want to watch you.” 

I stripped down and laid on my bed, watching my handsome boyfriend work. His shoulders were so broad and muscular. I wished I could have that, but I never would. It didn't bother me,however. My hand found my penis. I could see the profile of his face. His strong jaw, blond wavy hair, and chiseled nose. Daring turned and watched me, his eyes meeting my light brown ones. 

“Get back to work! I’m okay over here.” 

With a grin, he turned back to his paper. I stroked myself and thought about how lucky I was. I had found an amazing guy who cared about me as much as I cared about him. I could feel my orgasm building, and I jerked off quicker, finally shooting a long string of cum in the air which landed on my chest. Daring kept working while I cleaned myself up. I gave him a kiss and went to bed.

* * *

Saturday night finally came. 

I went back and forth from being a nervous wreck to being ecstatic. The last two nights, Daring had fingered my ass while he sucked my cock. First one finger, then two, and finally three. At first it hurt, but then it started to feel better. The thought of anal sex still frightened me. Three fingers was nowhere near the size of his cock. 

We picked up Chinese food and ate together while watching a movie. Next to the bed, something was in a bag, though I had no idea what was in it. Once the movie ended, he locked the door and smiled at me. “Are you ready?” 

“As ready as I ever will be.” 

We kissed and slowly undressed each other. I was used to feeling his face as we kissed by now. I ran my hand down his bare chest until I found his growing cock. His hand wrapped around my dick and we jerked each other off while we made out. 

Then, it was time. 

I was hard with excitement, but still a little nervous. I wasn’t sure if he would be able to fit inside me or not. I was a lot smaller, and I also worried whether I would be enough to satisfy him. Daring told me that he wanted me to go first and handed me the bag, which was filled with a bottle of lube, and condoms. 

“Take it nice and slow, this is my first time too! Remember?” 

"Yeah."

He waited while I rolled a condom over my dick. I used a generous amount of lube on his opening before positioning my cock at his entrance. Teasingly, I rubbed my penis all around his ass. “Humphrey, you have no idea how good that feels. I want you inside of me now!” 

Holding my cock firmly in my hand, I slowly pushed against his asshole and watched as the head of my dick entered him. Daring let out a loud groan and I almost pulled out. “No! Keep going, I want you to fuck me.” With his encouragement, I pushed farther and farther, watching my cock disappear up his ass. “Oh Humphrey, please go faster.” 

I held his hips, doing as told, thrusting in and out of him. He gripped the sheets tightly. Daring was so tight, and I've never felt anything compared to this, even when I was masturbating. I tried to settle into a rhythm, but I knew I wouldn’t be able to last long. My balls slapped against his as I fucked his ass. I still couldn't believe I was making love to Daring! He moaned again and squeezed his cock. He was harder than I ever remembered him being. 

His moans were coming faster now and they were putting me over the top. My speed increased and I could feel my balls swelling up, ready to drop their load. I slammed into him a bit rougher, and in return, he buried his face in my pillow so nobody would hear his cries of passion. I couldn’t hold back any longer, and I came harder than I've ever had. My thrusting slowed down until finally I wasn’t moving anymore, my hips against his and my cock buried in his ass. I pulled out and took off the condom before disposing of it. 

“That was incredible. Did it hurt?” I asked him. 

“No, it felt pretty good! I was scared I was going to cum too. That’s how wonderful it felt!” 

It was my turn now, and I got on my hands and knees. Part of me was scared, while another part of me couldn’t wait to feel my boyfriend inside of me. Daring put a condom on and coated my ass with lube. His finger penetrated me, and he finger-fucked my ass. 

It was decent, but would his cock feel even better? 

He pulled his finger out and I felt his dick against my entrance. The anticipation was killing me. “Tell me if it hurts, I'm going to try and go slow.” I nodded my agreement and he pushed himself inside. Immediately, he filled me, and his head was barely inside of me! I grunted and bit down on the pillow. Daring pushed slowly into me, going inch by inch. It hurt and I told him that I couldn’t take it, and that he needed to stop. 

Then, he pulled out and I felt empty. I caught my breath and told him to go again, his cock reentering me, going a little bit deeper this time. I was sweating now, the feelings being different, but durable. One second it hurt, then the next it felt great. He was gentle and only fucked me until I got used to the feeling of throbbing dick. 

“You okay?” he asked. I grunted yes and Daring smacked my ass, and I was groaning loudly in response. His speed was picking up now. I would feel completely full, and the next second, I would be totally empty as he thrust in and out of my ass. The pain was gone now, and I could manage it. Dare kept slapping my ass, which I loved He reached out and grabbed my hair with one hand. 

“Ahhh, s-slow down, your moving so quickly,” I moaned. I bit down on the pillow again, trying to muffle my moans. He pulled at my hair and thrust into me again. This was perfect! My best friend, my roommate, my boyfriend, was fucking my ass and I loved it! 

Most importantly, however, I loved him.

Daring's pace quickened, and I could sense he was going to cum. I started to buck my hips, pushing into him and making him fuck me deeper than before. His hand had let go of my hair, and he grabbed my thin hips. I felt his cock spasm inside of me and knew he was cumming. He continued fucking me until his cock was empty. When he pulled out, I collapsed onto the bed. 

I was an exhausted, sweaty mess. 

Daring took care of his condom, afterwards getting into bed next to me, our arms wrapping around each other. His mouth found mine and we kissed like it was the first time. 

We had done it! Our relationship had gone all the way. I kissed my boyfriend, and felt his tongue on mines. Eventually, our kisses died down and we just held onto one another. 

Daring spoke first, “That far more better than I could've ever imagined! I love you Humphrey.” 

“I love you too Dare.” 

We kissed again and drifted off into a peaceful sleep.


End file.
